Benzene, (trifluoromethyl)-

Data at NIST subscription sites:

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.


Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-138.87kcal/molCmScott, Douslin, et al., 1959hfusion=3.294±0.001 kcal/mol

Condensed phase thermochemistry data

Go To: Top, Gas phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Δfliquid-148.29kcal/molCcrGood, Lacina, et al., 1964ALS
Quantity Value Units Method Reference Comment
Δcliquid-805.29 ± 0.12kcal/molCcrGood, Lacina, et al., 1964ALS
Δcliquid-810.35kcal/molCcbSwarts, 1919Not corrected for CODATA value of ΔfH; ALS
Quantity Value Units Method Reference Comment
liquid64.890cal/mol*KN/AScott, Douslin, et al., 1959, 2DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
45.041298.15Scott, Douslin, et al., 1959, 2T = 12 to 365 K.; DH

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil375.0 ± 0.8KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus244.0KN/ADreisbach, 1955Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Ttriple244.14KN/AScott, Douslin, et al., 1959, 3Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple244.14KN/AMcCullough and Waddington, 1957Uncertainty assigned by TRC = 0.07 K; IPTS-48; TRC
Quantity Value Units Method Reference Comment
Tc559.9KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Δvap9.003kcal/molN/AMajer and Svoboda, 1985 
Δvap8.87kcal/molN/ABoublik, Fried, et al., 1984Based on data from 330. - 410. K. See also Basarová and Svoboda, 1991.; AC
Δvap8.98kcal/molVScott, Douslin, et al., 1959hfusion=3.294±0.001 kcal/mol; ALS

Enthalpy of vaporization

ΔvapH (kcal/mol) Temperature (K) Method Reference Comment
7.799375.2N/AMajer and Svoboda, 1985 
8.51343.N/ADykyj, Svoboda, et al., 1999Based on data from 328. - 413. K.; AC
7.55483.N/ADykyj, Svoboda, et al., 1999Based on data from 468. - 532. K.; AC
8.58338.IJadot and Fraiha, 1992Based on data from 323. - 384. K.; AC
8.53343.A,EBStephenson and Malanowski, 1987Based on data from 328. - 413. K. See also Potter and Saylor, 1951, Dykyj and Vanko, 1970, and Scott, Douslin, et al., 1959, 4.; AC
7.74475.N/AMousa, 1985Based on data from 460. - 530. K.; AC
8.46 ± 0.02334.CScott, Douslin, et al., 1959, 4AC
8.15 ± 0.02353.CScott, Douslin, et al., 1959, 4AC
7.79 ± 0.02375.CScott, Douslin, et al., 1959, 4AC
9.35256.N/AStull, 1947Based on data from 241. - 375. K.; AC
9.20290.N/AField and Saylor, 1946Based on data from 275. - 353. K.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    Tr = reduced temperature (T / Tc)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A (kcal/mol) β Tc (K) Reference Comment
334. - 375.13.100.2912559.9Majer and Svoboda, 1985 

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Temperature (K) A B C Reference Comment
328. - 412.324.088471305.612-55.858Scott, Douslin, et al., 1959, 4Coefficents calculated by NIST from author's data.
241. - 375.34.301261439.695-40.702Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

ΔsubH (kcal/mol) Temperature (K) Method Reference Comment
13.0227.MGSears and Hopke, 1948Based on data from 222. - 233. K.; AC

Enthalpy of fusion

ΔfusH (kcal/mol) Temperature (K) Method Reference Comment
3.2940244.14N/AScott, Douslin, et al., 1959, 2DH
3.291244.N/ADomalski and Hearing, 1996AC
2.866242.DSCAhmed and Eades, 1972AC

Entropy of fusion

ΔfusS (cal/mol*K) Temperature (K) Reference Comment
13.49244.14Scott, Douslin, et al., 1959, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

Bromine anion + Benzene, (trifluoromethyl)- = (Bromine anion • Benzene, (trifluoromethyl)-)

By formula: Br- + C7H5F3 = (Br- • C7H5F3)

Quantity Value Units Method Reference Comment
Δr12.6 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B
Δr25.7kcal/molPHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr23.cal/mol*KN/APaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr4.1 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
16.0423.PHPMSPaul and Kebarle, 1990gas phase; switching reaction,Thermochemical ladder(Br-)C6H5OH, Entropy change calculated or estimated; M

C7H4F3- + Hydrogen cation = Benzene, (trifluoromethyl)-

By formula: C7H4F3- + H+ = C7H5F3

Quantity Value Units Method Reference Comment
Δr387.1 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Quantity Value Units Method Reference Comment
Δr378.6 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Δr379.0 ± 5.0kcal/molIMRBBartmess and McIver Jr., 1979gas phase; B

C6H7N+ + Benzene, (trifluoromethyl)- = (C6H7N+ • Benzene, (trifluoromethyl)-)

By formula: C6H7N+ + C7H5F3 = (C6H7N+ • C7H5F3)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr11.8kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr26.cal/mol*KN/AMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
4.0300.PHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; Entropy change calculated or estimated; M

Nitric oxide anion + Benzene, (trifluoromethyl)- = (Nitric oxide anion • Benzene, (trifluoromethyl)-)

By formula: NO- + C7H5F3 = (NO- • C7H5F3)

Quantity Value Units Method Reference Comment
Δr35.kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes

Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

Mass spectrum
For Zoom
1.) Enter the desired X axis range (e.g., 100, 200)
2.) Check here for automatic Y scaling
3.) Press here to zoom

Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1990.
NIST MS number 118781

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Scott, Douslin, et al., 1959
Scott, D.W.; Douslin, D.R.; Messerly, J.F.; Todd, S.S.; Hossenlopp, I.A.; Kincheloe, T.C.; McCullough, J.P., Benzotrifluoride: Chemical thermodynamic properties and internal rotation, J. Am. Chem. Soc., 1959, 81, 1015-10. [all data]

Good, Lacina, et al., 1964
Good, W.D.; Lacina, J.L.; DePrater, B.L.; McCullough, J.P., A new approach to the combustion calorimetry of silicon and organosilicon compounds. Heats of formation of quartz, fluorosilicic acid, and hexamethyldisiloxane, J. Phys. Chem., 1964, 68, 579-586. [all data]

Swarts, 1919
Swarts, F., Etudes thermochimiques sur les combinaisons organiques fluorees, J. Chim. Phys., 1919, 17, 3-70. [all data]

Scott, Douslin, et al., 1959, 2
Scott, D.W.; Douslin, D.R.; Messerly, J.F.; Todd, S.S.; Hossenlopp, I.A.; Kincheloe, T.C.; McCullough, J.P., Benzotrifluoride: chemical thermodynamic properties and internal rotation, J. Am. Chem. Soc., 1959, 81, 1015-1017. [all data]

Dreisbach, 1955
Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]

Scott, Douslin, et al., 1959, 3
Scott, D.W.; Douslin, D.R.; Messerly, J.F.; Todd, S.S.; Hossenlopp, I.A.; Kincheloe, T.C.; McCullough, J.P., Benzotrifluoride: Chemical Thermodynamic Prop. and Internal Rotation, J. Am. Chem. Soc., 1959, 81, 1015-20. [all data]

McCullough and Waddington, 1957
McCullough, J.P.; Waddington, G., Melting-point purity determinations: limitations as evidenced by calorimetric studies in the melting region, Anal. Chim. Acta, 1957, 17, 80. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav, Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data, Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I . [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]

Jadot and Fraiha, 1992
Jadot, Roger; Fraiha, Mustapha, Isobaric vapor-liquid equilibrium of (trifluoromethyl)benzene with benzene, toluene, or chlorobenzene, J. Chem. Eng. Data, 1992, 37, 4, 509-511, https://doi.org/10.1021/je00008a031 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Potter and Saylor, 1951
Potter, John C.; Saylor, John H., The Vapor Pressures and Freezing Points of Some Organic Fluorine Compounds 1,2, J. Am. Chem. Soc., 1951, 73, 1, 90-91, https://doi.org/10.1021/ja01145a032 . [all data]

Dykyj and Vanko, 1970
Dykyj, J.; Vanko, A., Petrochemica, 1970, 10, 1, 3. [all data]

Scott, Douslin, et al., 1959, 4
Scott, D.W.; Douslin, D.R.; Messerly, J.F.; Todd, S.S.; Hossenlopp, I.A.; Kincheloe, T.C.; McCullough, J.P., Benzotrifluoride: Chemical Thermodynamic Properties and Internal Rotation 1, J. Am. Chem. Soc., 1959, 81, 5, 1015-1020, https://doi.org/10.1021/ja01514a001 . [all data]

Mousa, 1985
Mousa, A.H.N., The vapour pressures and saturated volumes of benzotrifluoride in the temperature range 460--530K., Journal of Fluorine Chemistry, 1985, 30, 1, 29-35, https://doi.org/10.1016/S0022-1139(00)80520-5 . [all data]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Field and Saylor, 1946
Field, Frank H.; Saylor, John H., The Vapor Pressures of Some Organic Fluorides 1,2, J. Am. Chem. Soc., 1946, 68, 12, 2649-2650, https://doi.org/10.1021/ja01216a068 . [all data]

Sears and Hopke, 1948
Sears, G.W.; Hopke, E.R., The Vapor Pressure of Benzotrifluoride Measured by the Rodebush Manometer, J. Phys. Chem., 1948, 52, 7, 1137-1142, https://doi.org/10.1021/j150463a004 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Ahmed and Eades, 1972
Ahmed, A.M.I.; Eades, R.G., Proton magnetic relaxation in toluene and some derivatives, J. Chem. Soc., Faraday Trans. 2, 1972, 68, 1623, https://doi.org/10.1039/f29726801623 . [all data]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Bartmess and McIver Jr., 1979
Bartmess, J.E.; McIver Jr., The Gas Phase Acidity Scale in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References